Compounds of hypervalent sulfur, isolable tetracoordinate sulfur (IV) species which we have called sulfuranes, have been found to be extraordinarily useful as synthetic reagents and intermediates in organic chemistry. A variety of studies of reactions expected to be of synthetic utility will be initiated using the wide range of structural types of isolable sulfuranes currently in hand or expected to be easily obtained using synthetic methods already developed in the research. Particular attention will be paid to reactions using sulfuranes as oxidizing or dehydrating agents. The use of chiral sulfuranes in stereospecific syntheses of epoxides will be explored. More soluble derivatives of ortho-bridged triarylcarbinol derivatives related to sesquixanthydrol, and of the 1,8-disubstituted 9-anthrylcarbocations earlier studied in these labs, will be prepared. Both classes of compounds have shown appreciable activity in the cancer chemotherapy screening program. Studies of the solvent cage effect will focus on the possible differences between radical pairs (X..Y) and ion pairs (X+Y-), nearest neighbors of identical composition, which are intermediates in reactions leading to free radicals and to those factors mediating the choice between homolytic and heterolytic bond cleavage of the X-Y molecule which is the precursor to these species.